Ripping / Management:
iTunes: Convenient, and fast (+ ripping is ripping, not rocket science). Digitised 2000 albums approx.
Format
ALAC: Convenient in terms of size. (I do not detect any differences between compressed lossless and non-compressed lossless).
Playback
Amarra Hifi OR BitPerfect
Depending on mood. Prefer the convenience, stability and UI (or non-UI) of BitPerfect, but I feel Amarra produces the best quality playback on the Mac (albeit buggier than BP).
Had extensive periods with these 2, and Audirvana.
Other
XLD, for fast and accurate conversion (usually from FLAC to ALAC or AIFF)
Audacity, for converting FLACs XLD has a problem with; Removing the odd click or unwanted "audio participation" from live recordings; Equalising LP transfers (when necessary).
iBatch for iTunes for metadata corrections. Unique flexibility plus integration with Discogs database, which is by far the more complete db for less commercial releases. New version out soon promises file/track management, music backup and archiving.